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BY-NC-ND 3.0 license Open Access Published by De Gruyter Open Access April 25, 2010

Equilibrium and kinetic study of the proton transfer reactions between nitroalkanes and strong organic bases — phosphazenes in tetrahydrofuran solvent

Iwona Binkowska, Włodzimierz Gałęzowski and Arnold Jarczewski
From the journal Open Chemistry

Abstract

Proton transfer reactions rates between carbon acids 1-nitro-1-(4-nitrophenyl)ethane (NPNE), 2-methyl-1-nitro-1-(4-nitrophenyl)propane (MNPNP)) and phosphazenes (BEMP, BTPP, P1-t-Oct) in tetrahydrofuran have been measured, and the activation parameters were determined. The results are compared with those previously obtained for P1-t-Bu phosphazene, guanidines and amidines.

[1] R. Schwesinger, J. Willaredt, H. Schlemper, M. Keller, D. Schmitt, H. Fritz, Chem. Ber. 127, 2435 (1994) http://dx.doi.org/10.1002/cber.1994127121510.1002/cber.19941271215Search in Google Scholar

[2] R. Schwesinger et al., Liebigs Ann. 1055 (1996) 10.1002/jlac.199619960705Search in Google Scholar

[3] R. Schwesinger, Angew. Chem. 105, 1420 (1994) http://dx.doi.org/10.1002/ange.1993105094010.1002/ange.19931050940Search in Google Scholar

[4] R. Schwesinger, Chimia 39, 269 (1985) 10.1016/S0021-5198(19)63701-7Search in Google Scholar

[5] R. Schwesinger, Nachr. Chem. Tech. Lab. 38, 1214 (1990) 10.1002/nadc.19900381005Search in Google Scholar

[6] L.A. Paquette, Encyclopedia of reagent for organic synthesis (John Wiley & Sons, Chichester, 1995) 6, 4110 Search in Google Scholar

[7] R. Schwesinger, H. Schlemper, Angew. Chem., Int. Ed. Engl. 26, 1168 (1987) 10.1002/anie.198711671Search in Google Scholar

[8] I. Kaljurand, T. Rodima, I. Leito, I. A. Koppel, R. Schwesinger, J. Org. Chem. 65, 6202 (2000) http://dx.doi.org/10.1021/jo005521j10.1021/jo005521jSearch in Google Scholar PubMed

[9] I. Leito, T. Rodima, I.A. Koppel, R. Schwesinger, V.M. Vlasov, J. Org. Chem. 62, 8479 (1997) http://dx.doi.org/10.1021/jo971301310.1021/jo9713013Search in Google Scholar PubMed

[10] I.A. Koppel et al., J. Phys. Chem. A 105, 9575 (2001) http://dx.doi.org/10.1021/jp012168s10.1021/jp012168sSearch in Google Scholar

[11] Ż. Wisıocka, I. Nowak, A. Jarczewski, J. Mol. Struct. 788, 152 (2006) http://dx.doi.org/10.1016/j.molstruc.2005.11.03110.1016/j.molstruc.2005.11.031Search in Google Scholar

[12] W. Gaıęzowski, A. Jarczewski, J. Chem. Soc. Perkin Trans. II, 1647 (1989) 10.1039/P29890001647Search in Google Scholar

[13] W. Gaıęzowski, A. Jarczewski, Can. J. Chem. 68, 2242 (1990) http://dx.doi.org/10.1139/v90-34510.1139/v90-345Search in Google Scholar

[14] W. Gaıęzowski, I. Grześkowiak, A. Jarczewski, J. Chem. Soc., Perkin Trans. 2, 1607 (1998) 10.1039/a801482eSearch in Google Scholar

[15] A. Jarczewski, C. D. Hubbard, J. Mol. Struct. 649, 287 (2003) http://dx.doi.org/10.1016/S0022-2860(03)00086-310.1016/S0022-2860(03)00086-3Search in Google Scholar

[16] M. Fletschinger, B. Zipperer, H. Fritz, H. Prinzbach, Tetrahedron Lett. 28, 2517 (1987) http://dx.doi.org/10.1016/S0040-4039(00)95456-X10.1016/S0040-4039(00)95456-XSearch in Google Scholar

[17] L. Melander, W.H. Saunders Jr., Reaction rates of isotopic molecules (John Wiley and Sons, NewYork, 1980) 287 Search in Google Scholar

[18] G. Bergson, Chem. Scr. 8, 145 (1975) Search in Google Scholar

[19] E.S. Lewis, L.H. Funderburk, J. Am. Chem. Soc. 89, 2322 (1967) http://dx.doi.org/10.1021/ja00986a01310.1021/ja00986a013Search in Google Scholar

[20] E.S. Lewis, L.H. Funderburk, J. Am. Chem. Soc. 86, 2531 (1964) http://dx.doi.org/10.1021/ja01066a05510.1021/ja01066a055Search in Google Scholar

[21] R.P. Bell, The Proton in Chemistry, 2nd edition (Chapman and Hall, London, 1973) Search in Google Scholar

Published Online: 2010-4-25
Published in Print: 2010-6-1

© 2010 Versita Warsaw

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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